The present proposal outlines nine specific projects designed to elucidate unanswered questions in the shikimic acid pathway. These include the stereo-specific total synthesis of chorismic acid, investigation of the mechanism of chorismate synthetase, the total synthesis of optically active phenylalanine epoxide, the synthesis of gliotoxin, and confirmation of the structure and bio-synthesis of the aminoacid antibiotics anticapsin and bacilysin.